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MDW (Chicago) to OAK (Oakland) Flights $281.8

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Cheap MDW to OAK Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Oakland (MDW to OAK)

Question : Is there another local airport to fly into besides Metropolitan Oakland International Airport (OAK)?
Answer : Metropolitan Oakland International Airport is a great airport, but there is a cheaper option – San Francisco International Airport. It’s just 12 miles away and flights are being booked 29% cheaper over the coming two months.

Question : Who struggles with getting their passengers to Metropolitan Oakland International Airport (OAK) on time?
Answer : If you're flying XOJET to Oakland from Chicago, you may be tardy as they're delayed 100% of the time. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : What's the likelihood of you being delayed on this route?
Answer : The best measurement of overall promptness combines both on-time percentage and total delay minutes. MDW to OAK currently has 2 stars out of 5, earning it one of the lower scores in the world.

Question : Should you take that vacation to Oakland in the next 30 days?
Answer : Aug 2nd has seen bookings (as of Jul 24th) as cheap as $312. That comes in 53% below the average price for this route. Saving on flight costs means you'll have more cash to spend on your trip.

Question : Which airline has been the most dependable in getting passengers to their destination on schedule?
Answer : Southwest Airlines leads the way with a 74% on-time rate. Spend as little time in an airport as necessary by flying with Southwest Airlines. Note that if they do have a delay, it usually lasts about half an hour.

Question : Which airline is offering the cheapest flight from MDW to OAK?
Answer : Prices are hitting highs of $949 over the next three months when flying to OAK from MDW. Check out Delta Air Lines, as they have been booking customers at just $282.

Question : On a daily basis, how many different flight times are available from Chicago Midway International Airport (MDW) to Metropolitan Oakland International Airport (OAK)?
Answer : Of course the day matters, but on average, two different flight times exist when you fly from MDW to OAK. You won't have as many options on this route as most other routes departing the United States.